Iodoethane → (3S)-1,3-diethyl-6-fluoro-4-(4-methoxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-one

HRID 898222ノート

反応式

HRID 898222 の反応式
[CH2:1]([C@@H:3]1[N:12]([C:13](=[O:22])[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([F:23])[CH:10]=2)[NH:5][C:4]1=[O:24])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].C(=O)([O-])[O-].[K+].[K+].I[CH2:38][CH3:39]>CC(C)=O>[CH2:38]([N:5]1[C:6]2[C:11](=[CH:10][C:9]([F:23])=[CH:8][CH:7]=2)[N:12]([C:13](=[O:22])[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[C@@H:3]([CH2:1][CH3:2])[C:4]1=[O:24])[CH3:39]

参加物

6

反応物 4

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 11430Potassium CarbonateHCID 69223582(3S)-3-ethyl-6-fluoro-4-(4-methoxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-one

生成物 1

HCID 69222645(3S)-1,3-diethyl-6-fluoro-4-(4-methoxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-one収率 75%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

反応条件

温度
51 °C

実験手順

To a stirred solution of (3S)-3-ethyl-6-fluoro-4-(4-methoxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-one (0.25 g, 0.76 mmol) in acetone (6 mL) under nitrogen was added cesium carbonate (0.133 g, 0.41 mmol), potassium carbonate (0.057 g, 0.41 mmol) and iodoethane (0.20 mL, 0.39 g, 2.5 mmol). The reaction was stirred at 51° C. for 4 h. The solvent was evaporated, and the residue was partitioned between methylene chloride and water. The organic layer was separated and washed with water. The combined organic layers were dried over magnesium sulfate and concentrated in vacuo. The product was purified via Biotage Horizon® (SiO2, gradient from 4% EtOAc/hexane to 38% EtOAc/hexane) to yield 0.19 g (75%) of (3S)-1,3-diethyl-6-fluoro-4-(4-methoxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-one. MS (ESI) m/z 357 ([M+H]+).

後処理

  1. customThe solvent was evaporated
  2. customthe residue was partitioned between methylene chloride and water
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materialThe combined organic layers were dried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe product was purified via Biotage Horizon® (SiO2, gradient from 4% EtOAc/hexane to 38% EtOAc/hexane)

出典と根拠

ORDレコード
ord-cf21503581eb46188be3a7521397a30e
出典データセット
uspto-grants-2008_04
特許番号
US07351709B2

反応ノート

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